(4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate

Base Information

Chemical Name:(4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate
CAS No.:1448786-13-7
Molecular Formula:C₅₁H₈₄O₁₀
Molecular Weight:857.222
Hs Code.:

Synonyms:(4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate

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Chemical Property of (4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate

Chemical Property:

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Technology Process of (4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate

There total 21 articles about (4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1448786-00-2
(4R,6R,8R,10S,12R)-12-(benzyloxy)-6,8,10-tris(methoxymethoxy)heptacos-1-en-4-ol

: 1448786-13-7
(4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1002/ejoc.201201309

Reference yield:

: 1448785-85-0
(R)-[(nonadec-1-en-4-yloxy)methyl]benzene

: 1448786-13-7
(4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate

Guidance literature:: Multi-step reaction with 18 steps

1.1: 2,6-dimethylpyridine; osmium(VIII) oxide; sodium periodate / 1,4-dioxane; water / 1 h / 20 °C

2.1: titanium tetrachloride / dichloromethane / 2 h / -78 °C / Inert atmosphere

3.1: triethylamine; dmap / dichloromethane / 5 h / 20 °C

4.1: N-iodo-succinimide / acetonitrile / 4 h / -40 - 0 °C

5.1: potassium carbonate / methanol / 1 h / 25 °C

6.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / 0 °C

6.2: 12 h / 0 - 20 °C

7.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere

7.2: 1.33 h / -20 - 20 °C

8.1: triethylamine; dmap / dichloromethane / 6 h / 20 °C

9.1: N-iodo-succinimide / acetonitrile / 3 h / -40 - 0 °C

10.1: potassium carbonate / methanol / 1 h / 20 °C

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C / Cooling with ice

12.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

12.2: 2.5 h / -20 - 20 °C

13.1: triethylamine; dmap / dichloromethane / 6 h / 20 °C

14.1: N-iodo-succinimide / acetonitrile / 4 h / -40 - 0 °C

15.1: potassium carbonate / methanol / 1 h / 20 °C

16.1: N-ethyl-N,N-diisopropylamine; chloromethyl methyl ether / dichloromethane / 6 h / 20 °C / Cooling with ice

17.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere

17.2: 2 h / -20 - 20 °C

18.1: triethylamine; dmap / dichloromethane / 6 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium periodate; N-iodo-succinimide; copper(l) iodide; osmium(VIII) oxide; titanium tetrachloride; sodium hydride; potassium carbonate; chloromethyl methyl ether; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201201309

Reference yield:

: 1448785-86-1
(4R,6R)-6-(benzyloxy)henicos-1-en-4-ol

: 1448786-13-7
(4R,6S,8S,10S,12R)-12-(benzyloxy)-10-(4-methoxybenzyloxy)-6,8-bis(methoxymethoxy)heptacos-1-en-4-yl tert-butyl carbonate

Guidance literature:: Multi-step reaction with 16 steps

1.1: triethylamine; dmap / dichloromethane / 5 h / 20 °C

2.1: N-iodo-succinimide / acetonitrile / 4 h / -40 - 0 °C

3.1: potassium carbonate / methanol / 1 h / 25 °C

4.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / 0 °C

4.2: 12 h / 0 - 20 °C

5.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere

5.2: 1.33 h / -20 - 20 °C

6.1: triethylamine; dmap / dichloromethane / 6 h / 20 °C

7.1: N-iodo-succinimide / acetonitrile / 3 h / -40 - 0 °C

8.1: potassium carbonate / methanol / 1 h / 20 °C

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C / Cooling with ice

10.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

10.2: 2.5 h / -20 - 20 °C

11.1: triethylamine; dmap / dichloromethane / 6 h / 20 °C

12.1: N-iodo-succinimide / acetonitrile / 4 h / -40 - 0 °C

13.1: potassium carbonate / methanol / 1 h / 20 °C

14.1: N-ethyl-N,N-diisopropylamine; chloromethyl methyl ether / dichloromethane / 6 h / 20 °C / Cooling with ice

15.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere

15.2: 2 h / -20 - 20 °C

16.1: triethylamine; dmap / dichloromethane / 6 h / 20 °C

With dmap; N-iodo-succinimide; copper(l) iodide; sodium hydride; potassium carbonate; chloromethyl methyl ether; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201201309